US2664438A - Dialkyl 3-dodecyloxypropane-1-phosphonate - Google Patents
Dialkyl 3-dodecyloxypropane-1-phosphonate Download PDFInfo
- Publication number
- US2664438A US2664438A US194022A US19402250A US2664438A US 2664438 A US2664438 A US 2664438A US 194022 A US194022 A US 194022A US 19402250 A US19402250 A US 19402250A US 2664438 A US2664438 A US 2664438A
- Authority
- US
- United States
- Prior art keywords
- dialkyl
- dodecyloxypropane
- phosphonate
- parts
- phosphite
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- QWHQFLUIWXUADU-UHFFFAOYSA-N 3-dodecoxypropylphosphonic acid Chemical compound CCCCCCCCCCCCOCCCP(=O)(O)O QWHQFLUIWXUADU-UHFFFAOYSA-N 0.000 title claims description 3
- NSRJCKNAJOEJMR-UHFFFAOYSA-N 1-prop-2-enoxydodecane Chemical compound CCCCCCCCCCCCOCC=C NSRJCKNAJOEJMR-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- -1 Diethyl 3 dodecyloxypropane-l-phosphonate Chemical compound 0.000 description 1
- FQFXNZOXYYZTHD-UHFFFAOYSA-N P(O)(O)=O.CCC Chemical class P(O)(O)=O.CCC FQFXNZOXYYZTHD-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Definitions
- This invention relates to the preparation of certain dialkyl propane phosphonates by the free-radical-catalyzed reaction of a dialkyl phosphite and allyl dodecyl ether.
- the alkyl groups of the phosphite may each contain from 1 to 4 carbon atoms.
- Example 45.28 parts of allyl dodecyl ether are heated with 56 parts of diethyl phosphite at 80-85 C. for 38 hours during which time 1.2 parts of benzoyl peroxide are added in 4 equal increments at 0, 5.5, 14. and 23 hours of elapsed reaction time.
- the reaction mixture is fractionally distilled under reduced pressure, 41.9 parts of unreacted diethyl phosphite and 23.9 parts of allyl dodecyl ether being recovered, then 30.2 parts of high-boiling liquid residue (b. 192/0.9 mm.) consisting of diethyl 3-dodecycloxypropane-1-phosphonate.
- the chemicals may be used as plasticizers for polyvinyl chloride.
- the products have in the molecule thereof the components of one molecule of the phosphite and one molecule of the ether.
- the temperature and time of the reaction may vary widely depending on the source of free radicals which may be ultra-violet light or a catalyst of the class of peroxidic com ounds (e. g., benzoyl peroxide, tert.-butyl hydroperoxide, acetyl peroxide, hydrogen peroxide, potassium peroxysulfate), hydrazine and substituted hydrazines, azobenzene, and metal alkyls (e. g., sodium ethyl and lead tetraethyl), the amount of such eatalyst compound employed being usually in the range of from 0.1 to 15.0% by weight of the reactant mixture.
- a catalyst of the class of peroxidic com ounds e. g., benzoyl peroxide, tert.-butyl hydroperoxide, acetyl peroxide, hydrogen peroxide, potassium peroxysulfate
- reaction temperatures are preferably C. to C. (when using benzoyl peroxide), and the time preferably 2 to 48 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Patented Dec. 29, 1953 UNITED STATES DIALKYL 3-DODECYLOXYPROPANE-1- PHOSPHQNATE Elbert C. Ladd and Merlin N. J., assignors to United P. Harvey, Passaic, States Rubber Company, New York, N. Y., a corporation of New Jersey No Drawing. Application November 3, 1950, Serial No. 194,022
2 Claims.
This invention relates to the preparation of certain dialkyl propane phosphonates by the free-radical-catalyzed reaction of a dialkyl phosphite and allyl dodecyl ether. The alkyl groups of the phosphite may each contain from 1 to 4 carbon atoms.
This application is a continuation-in-part of application Serial No. 38,188, filed July 12, 1948, now abandoned.
The following example is illustrative of the manner of preparation.
Example 45.28 parts of allyl dodecyl ether are heated with 56 parts of diethyl phosphite at 80-85 C. for 38 hours during which time 1.2 parts of benzoyl peroxide are added in 4 equal increments at 0, 5.5, 14. and 23 hours of elapsed reaction time. The reaction mixture is fractionally distilled under reduced pressure, 41.9 parts of unreacted diethyl phosphite and 23.9 parts of allyl dodecyl ether being recovered, then 30.2 parts of high-boiling liquid residue (b. 192/0.9 mm.) consisting of diethyl 3-dodecycloxypropane-1-phosphonate.
Analysis-Calculated: C, 62.60; H, 11.34; P. 8.50. Found: C, 63.02; H, 11.29; P. 7.59.
The chemicals may be used as plasticizers for polyvinyl chloride.
The products have in the molecule thereof the components of one molecule of the phosphite and one molecule of the ether.
The temperature and time of the reaction may vary widely depending on the source of free radicals which may be ultra-violet light or a catalyst of the class of peroxidic com ounds (e. g., benzoyl peroxide, tert.-butyl hydroperoxide, acetyl peroxide, hydrogen peroxide, potassium peroxysulfate), hydrazine and substituted hydrazines, azobenzene, and metal alkyls (e. g., sodium ethyl and lead tetraethyl), the amount of such eatalyst compound employed being usually in the range of from 0.1 to 15.0% by weight of the reactant mixture.
The reaction temperatures are preferably C. to C. (when using benzoyl peroxide), and the time preferably 2 to 48 hours.
Having thus described our invention, what we claim and desire to protect by Letters Patent is:
1. A dialkyl 3-dodecyloxypropane-l-phosphonate.
2. Diethyl 3 dodecyloxypropane-l-phosphonate.
ELBERT C. LADD. MERLIN P. HARVEY.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,440,800 Hanford II May 4, 1948 2,478,390 Hanford et al Aug. 9, 1949 2,492,994 Harman et a1 Jan. 3, 1950 2.500.022 Brown Mar. '7. 150 2,535,172 Tawney Dec. 26, 1950
Claims (1)
1. A DIALKY 3-DODECYLOXYPROPANE-1-PHOSPHONATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US194022A US2664438A (en) | 1950-11-03 | 1950-11-03 | Dialkyl 3-dodecyloxypropane-1-phosphonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US194022A US2664438A (en) | 1950-11-03 | 1950-11-03 | Dialkyl 3-dodecyloxypropane-1-phosphonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2664438A true US2664438A (en) | 1953-12-29 |
Family
ID=22715988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US194022A Expired - Lifetime US2664438A (en) | 1950-11-03 | 1950-11-03 | Dialkyl 3-dodecyloxypropane-1-phosphonate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2664438A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096238A (en) * | 1960-12-20 | 1963-07-02 | Monsanto Chemicals | Omicron-(halophenyl) phosphonothioates |
| US4264532A (en) * | 1977-12-19 | 1981-04-28 | Takashi Tsuruoka | Process for preparing D,L-2-amino-4-methylphosphinobutyric acid |
| US20070123492A1 (en) * | 2003-04-09 | 2007-05-31 | Prestwich Glenn D | Analogs of lysophosphatidic acid and methods of making and using thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2440800A (en) * | 1942-04-10 | 1948-05-04 | Du Pont | Halogenated hydrocarbons and method for their preparation |
| US2478390A (en) * | 1947-12-18 | 1949-08-09 | Du Pont | Polymerization of polymerizable mono-olefinic hydrocarbons in the presence of saturated aliphatic esters of inorganic oxy acids of phosphorus, sulfur, and silicon |
| US2492994A (en) * | 1948-05-11 | 1950-01-03 | Shell Dev | Bituminous compositions |
| US2500022A (en) * | 1946-08-06 | 1950-03-07 | Oldbury Electrochemical Compan | Dialkyl alkoxy methane phosphonates and method of preparation |
| US2535172A (en) * | 1949-02-25 | 1950-12-26 | Us Rubber Co | Dialkyl 2-alkoxy-ethanephosphonates and process of preparing |
-
1950
- 1950-11-03 US US194022A patent/US2664438A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2440800A (en) * | 1942-04-10 | 1948-05-04 | Du Pont | Halogenated hydrocarbons and method for their preparation |
| US2500022A (en) * | 1946-08-06 | 1950-03-07 | Oldbury Electrochemical Compan | Dialkyl alkoxy methane phosphonates and method of preparation |
| US2478390A (en) * | 1947-12-18 | 1949-08-09 | Du Pont | Polymerization of polymerizable mono-olefinic hydrocarbons in the presence of saturated aliphatic esters of inorganic oxy acids of phosphorus, sulfur, and silicon |
| US2492994A (en) * | 1948-05-11 | 1950-01-03 | Shell Dev | Bituminous compositions |
| US2535172A (en) * | 1949-02-25 | 1950-12-26 | Us Rubber Co | Dialkyl 2-alkoxy-ethanephosphonates and process of preparing |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096238A (en) * | 1960-12-20 | 1963-07-02 | Monsanto Chemicals | Omicron-(halophenyl) phosphonothioates |
| US4264532A (en) * | 1977-12-19 | 1981-04-28 | Takashi Tsuruoka | Process for preparing D,L-2-amino-4-methylphosphinobutyric acid |
| US20070123492A1 (en) * | 2003-04-09 | 2007-05-31 | Prestwich Glenn D | Analogs of lysophosphatidic acid and methods of making and using thereof |
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